Afternoon Deserts

by Linda

What’s your gender? Woman
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? CPA/Controller
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Hot and Cold
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 2

Afternoon Deserts

How long ago did this hookup happen? Today

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Jess is the Vice President of Sales at the company I worked for prior to leaving in December. I have been in a sexless marriage for 6 years by my choice, I love my husband but I just lost the desire. Jessie is 6 foot 2 inches, with a solid build and a slight bulge in his midsection. We have worked together through 2 mergers and have always gotten along. We have shared the fact that we love our spouses but don’t feel sexual toward them. His wife travels and shops a lot, my husband works a lot.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jessie contacted me via email asking if we could meet for lunch to review a final project I was finishing for him. It’s been 2 months since I left and I replied “Sure.” as I want to wrap this up. We met and had lunch at a rather nice restaurant downtown and we went through the information and analysis I had put together. As I was gathering the laptop up from him, Jessie held my hand, which shocked me. I had seen the look he was giving me before in my life, that look when a boy or man says I want to fuck you. I rolled my eyes and then said “Really?” Jessie replied, “Tell me you’re not attracted to me?” Well, he knew I was and I felt his other hand under the table and table cloth moving up my inner thigh. “I think we need to go through this analysis again,” Jessie said. I thought quickly and finally decided what the hell, why not? Let’s see if he can turn me on.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Across the street was a 5-star hotel and Jessie walked me over to the hotel and got a room for us. It was about 1 pm and I called work on the cell phone to let them know I would be out the rest of the afternoon. Jessie and I rode the elevator up to the 8th floor, and during the ride, he held my hand. It felt good and I felt a stirring inside of me. We got off the elevator and walked hand in hand to the room and Jessie unlocked it, opened the door and held it for me.

I walked in first, then Jessie who locked and bolted the door. The room was terrific. It had a kitchen, the main living room with two couches and a nice large TV and then a bedroom with a canopy king size bed. It was plush and I knew it would be having stayed here in my earlier married life with my husband.

Jessie came to me in the living room, drawing me near to him and pulling me close. I wrapped my arms around his back, holding him close and our lips met. We began to make out and then removed our shirts, my bra, his tee shirt, and I undid his belt, his pant hook, and zipper, removing his pants and boxers. Jessie removed my pants and panties quickly.

We embraced again naked and Jessie kissed me. He then led me to a soft and plush chair and had me sit. He spread my legs over the sides and knelt down in front of me. Jessie then gave me probably the best oral sex on my pussy I have ever had. He worked my clit and my cunt until I was ready to have an orgasm. It had been a LONG time since I had wanted to be fucked. After fifteen minutes of oral, Jessie came up, kissing me and making out, letting me taste my wetness as our tongues enjoyed each other.

I stood up finally, and took Jessie by the hand and took him into the king size canopy bed in the bedroom. My pussy was hungry, aching to be filled and to be satisfied. Desiring to feel Jessie’s dick penetrate inside of me and fill me up, exciting and exhilarating me. We got under the covers, and I stroked his hard dick a few times. I then pushed the covers back, laid Jessie on his back, and I mounted him. I played with his dick, having it rub my pussy hole and all around that area until I was deeply desirous to have it in me.

I leaned forward and using only my cunt, I guided that monster penis inside of my pussy. At first, I only let the head enter me, and I moved Jessie’s dick head in and out several times before driving his thick big penis deep inside of me. I moaned in pleasure as Jessie’s hard dick provided me with a complete sense of fullness as I drove it all the way inside of me. Damn, it felt good to push boundaries again in my life, I hadn’t fucked a man I hadn’t been married for 30 years and this was heavenly.

I began to trot like in a saddle, Jessie’s dick driving into me as I sat back and coming out as I leaned forward. Jessie’s hands raised up and he began playing with my boobs and squeezing my tits. He figured out quickly I liked the sides of my boobs rubbed when I am having sex.

I varied the pace, in total control now. I would increase the pace, then slow down, then speed up, then stop and when I stopped, Jessie would gently drive his penis all the way inside my pussy and then slightly out and back in for six to eight times, letting me just feel his dick fill up my pussy. I felt my flame beginning to burn, I felt how smooth his dick and my pussy were together and I started to fuck faster. Faster and faster until the nerves in my body exploded in pure pleasure, with euphoria spreading across my complete body but emanating from my pussy. Jessie held me tight as I felt his penis bulge, throb and then I felt his warm cum shoot out of the end of his dick. I felt Jessie cum in me again, and then again, his cum warming my pussy even more. I feel unto his chest and began kissing him and squeezing his dick with my pussy.

We waited around and his finger found my pussy and my mouth his dick making him hard again. We fucked again about an hour later, I was indeed ready to fuck and I rode Jessie again. Then we screwed around touching more and getting both of us turned on again, though this time it took Jessie about 2 hours to get hard, and then I let Jessie have his way, the missionary position. It felt incredible, not as good as riding, but still terrific. Jessie fucked me for a good forty-five minutes in the missionary and at the end, was pounding me consistently though not fast. We came together making this time probably the best of the three, and we then kissed and fell asleep together in that wonderful bed of sexual fulfillment for both of us.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Jessie is laying in the bed, just waking up as I am typing this. I am still horny after 6 years and I am hungry, ready for that wonderful dick of his to pleasure me. I am going to end this, walk over, and ride my Jessie James (not his last name) so he can rob this married woman of her 30 years of fidelity. After that, not sure, probably head home and see if this is a one-time thing, or if Jessie wants a regular hook up. I am definitely good for a regular hook up for a while

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, To feel more desirable, I was feeling lonely, Just wanted a good fuck session after 6 years of none. I was finally ready and Jessie was there.

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one, maybe my husband later tonight to see what he says.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Sex was incredible! No talking during sex, just sex. Our bodies and hands communicated what we both wanted.

What was the WORST thing about this hookup? It will end for tonight.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I felt like a woman again, horny, longing to have my pussy filled by a man’s hard penis, ready to take his ejaculate as I have my orgasm.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Hope we find time to fuck each other some more!

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Hey, when you need it, you need it and better to do it with someone you’re attracted to and know.

What do you think about the Casual Sex Project? It is what it is I guess.

You have a hookup story to share? Submit it here!